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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2275085Generated: October 26, 2026

Water → 8-(2-(diethylamino)ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/reaction/2275085

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
ReactantDiethylaminoethyl chlorideHCID 13364—
Reactant8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66833861—
SolventDimethylacetamideHCID 31374—
Product8-(2-(diethylamino)ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 5458086733%

Reaction Conditions

Temperature100 °C

Reaction Steps

8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 25 mg, 0.083 mmol) was dissolved in N,N-dimethylacetamide (1 mL), added with 2-chloroethyldiethylamine (16 mg, 1.1 eq.) and cesium carbonate (54 mg, 2 eq.) in order and stirred at 100° C. for 4 hr. The reaction solution was poured over water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by amino silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (11 mg, 32%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126931B2
Source datasetuspto-grants-2015_09
ORD IDord-69b256b181144655bc12403c5850f623
Source noteuspto-grants-2015_09